1,2,4-Trimethylbenzene → 2-Ethyl-4-methyl-5-(4-methylphenyl)-4-pentenal

HRID 2408251Notes

Reaction equation

HRID 2408251 reaction equation
C([O:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13](C)=[CH:12][CH:11]=1)C(C)=C)C=CC.[C:17]1([C:19](=[CH:21][C:22](=[CH:24][CH:25]=1)[CH3:23])C)[CH3:18]>>[CH2:15]([CH:10]([CH2:11][C:12]([CH3:13])=[CH:18][C:17]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:19]=1)[CH:6]=[O:5])[CH3:14]

Participants

3

Reactant 2

HCID 72471,2,4-TrimethylbenzeneHCID 673307901-[1-(2-Butenyloxy)-2-methyl-2-propenyl]-4-methylbenzene

Product 1

HCID 767741622-Ethyl-4-methyl-5-(4-methylphenyl)-4-pentenalYield 36%

Procedure

The 1-[1-(2-butenyloxy)-2-methyl-2-propenyl]-4-methylbenzene (50.12 g, 0.232 mol), [RuCl2(PPh3)3] (400 mg), BHT (50 mg) and pseudo-cumene (60 ml) were heated together in an autoclave placed in an oil bath at 180° C. for 5 hours. After cooling to room temperature, the pseudo-cumene was distilled off (40° C./5 mbar) and the residue chromatographed on silica gel (eluent: heptanes/ethyl acetate 50:1 to 25:1), then distilled under vacuum through a 20-cm Widmer column. 18.1 g of the desired product were obtained (yield=36%). B.P.=80° C./0.001 mbar

Workup

  1. distillationthe pseudo-cumene was distilled off (40° C./5 mbar)
  2. customthe residue chromatographed on silica gel (eluent: heptanes/ethyl acetate 50:1 to 25:1)
  3. distillationdistilled under vacuum through a 20-cm Widmer column

Sources & evidence

ORD record
ord-633cca2068564d40bfd5e1e1be0dd3a8
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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